# 1990 Virginia Slims of Chicago – Singles

Martina Navratilova defeated Manuela Maleeva in the final, 6–3, 6–2 to win the singles tennis title at the 1990 Virginia Slims of Chicago.
Zina Garrison was the defending champion, but lost in the semifinals to Maleeva.

## Seeds

* Martina Navratilova (champion)
* Zina Garrison-Jackson (semifinal)
* Arantxa Sánchez Vicario (first round)
* Monica Seles (first round)
* Manuela Maleeva-Fragniere (final)
* Natalia Zvereva (first round)
* Laura Gildemeister (second round)
* Pam Shriver (quarterfinals)

## Draw
### Key

* Q = Qualifier
* WC = Wild card
* LL = Lucky loser
* Alt = Alternate
* SE = Special exempt
* PR = Protected ranking
* ITF = ITF entry
* JE = Junior exempt
* w/o = Walkover
* r = Retired
* d = Defaulted
* SR = Special ranking

### Finals

| Semifinals | Semifinals | Semifinals | Semifinals | Final | Final | Final | Final |
| 1 | Martina Navratilova | 6 | 6 | | | | |
| 8 | Pam Shriver | 4 | 3 | | | | |
| 8 | Pam Shriver | 4 | 3 | 1 | Martina Navratilova | 6 | 6 |
| | | | | 5 | Manuela Maleeva-Fragniere | 3 | 2 |
| 5 | Manuela Maleeva-Fragniere | 6 | 6 | 5 | Manuela Maleeva-Fragniere | 3 | 2 |
| 2 | Zina Garrison-Jackson | 2 | 0 | | | | |

### Top half

| First round | First round | First round | First round | First round | Second round | Second round | Second round | Second round | Second round | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Semifinals | Semifinals | Semifinals | Semifinals |
| 1 | M Navratilova | 6 | 6 | | | | | | | | | | | | | | |
| | A Temesvári-Trunkos | 1 | 3 | | 1 | M Navratilova | 6 | 6 | | | | | | | | | |
| Q | A Keller | 6 | 6 | | | A White | 0 | 0 | | | | | | | | | |
| | A White | 7 | 7 | | | | | | | 1 | M Navratilova | 6 | 6 | | | | |
| Q | T Whitlinger | 3 | 6 | 6 | | | | | | Q | T Whitlinger | 0 | 1 | | | | |
| | H Na | 6 | 3 | 1 | Q | T Whitlinger | 0 | 6 | 6 | | | | | | | | |
| | K Rinaldi | 7 | 3 | 6 | | K Rinaldi | 6 | 4 | 3 | | | | | | | | |
| 6 | N Zvereva | 5 | 6 | 1 | | | | | | | | | | 1 | Martina Navratilova | 6 | 6 |
| 3 | A Sánchez Vicario | 3 | 6 | | | | | | | | | | | 8 | Pam Shriver | 4 | 3 |
| Q | L Harvey-Wild | 6 | 7 | | Q | L Harvey-Wild | 6 | 6 | | | | | | | | | |
| | N Provis | 1 | 6 | 7 | | N Provis | 4 | 4 | | | | | | | | | |
| | A Grossman | 6 | 1 | 6 | | | | | | Q | L Harvey-Wild | 1 | 2 | | | | |
| | S Sloane | 7 | 7 | | | | | | | 8 | P Shriver | 6 | 6 | | | | |
| | L Ferrando | 5 | 6 | | | S Sloane | 3 | 4 | | | | | | | | | |
| | A Henricksson | 2 | 2 | | 8 | P Shriver | 6 | 6 | | | | | | | | | |
| 8 | P Shriver | 6 | 6 | | | | | | | | | | | | | | |

### Bottom half

| First round | First round | First round | First round | First round | Second round | Second round | Second round | Second round | Second round | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Semifinals | Semifinals | Semifinals | Semifinals |
| 5 | M Maleeva-Fragniere | 6 | 6 | | | | | | | | | | | | | | |
| LL | L Allen | 3 | 3 | | 5 | M Maleeva-Fragniere | 6 | 7 | | | | | | | | | |
| | A Smith | 6 | 3 | 1 | | P Fendick | 4 | 5 | | | | | | | | | |
| | P Fendick | 3 | 6 | 6 | | | | | | 5 | M Maleeva-Fragniere | 6 | 6 | | | | |
| | A Minter | 6 | 3 | 1 | | | | | | | R Fairbank-Nideffer | 1 | 0 | | | | |
| | C Kohde-Kilsch | 3 | 6 | 6 | | C Kohde-Kilsch | 3 | 6 | 3 | | | | | | | | |
| | R Fairbank-Nideffer | 6 | 6 | | | R Fairbank-Nideffer | 6 | 3 | 6 | | | | | | | | |
| 4 | M Seles | 3 | 4 | | | | | | | | | | | 5 | Manuela Maleeva-Fragniere | 6 | 6 |
| 7 | L Gildemeister | 6 | 6 | 6 | | | | | | | | | | 2 | Zina Garrison-Jackson | 2 | 0 |
| | G Rush | 1 | 7 | 4 | 7 | L Gildemeister | 1 | 7 | 5 | | | | | | | | |
| | N Tauziat | 6 | 6 | | | N Tauziat | 6 | 6 | 7 | | | | | | | | |
| | I Cueto | 4 | 1 | | | | | | | | N Tauziat | 3 | 5 | | | | |
| | L McNeil | 7 | 7 | | | | | | | 2 | Z Garrison-Jackson | 6 | 7 | | | | |
| | T Phelps | 5 | 6 | | | L McNeil | 3 | 2 | | | | | | | | | |
| | M Pierce | 4 | 4 | | 2 | Z Garrison-Jackson | 6 | 6 | | | | | | | | | |
| 2 | Z Garrison-Jackson | 6 | 6 | | | | | | | | | | | | | | |